Title: Middletown, NY Cottage Rentals from $181 | Expedia.com [Middletown Travel Guide](https://expedia.com/Middletown.dx8864)[Hotels in Middletown](https://expedia.com/Middletown-Hotels.d8864.Travel-Guide-Hotels)[Vacation Rentals in Middletown](https://expedia.com/Middletown-Vacation-Rentals.d8864.Travel-Guide-VacationRentals)[Flights to Middletown](https://expedia.com/Cheap-Flights-To-Middletown.d8864.Travel-Guide-Flights)[Things to do in Middletown](https://expedia.com/Things-To-Do-In-Middletown.d8864.Travel-Guide-Activities)[Car Rentals in Middletown](https://expedia.com/Car-Rentals-In-Middletown.d8864.Car-Rental-Guide)[Middletown Vacation Packages](https://expedia.com/Middletown.d8864.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/8005/8b2c54c4-af30-4521-9b56-3bdf0a8d1a15.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Vincent Ramundo ![](https://images.trvl-media.com/place/8005/8b2c54c4-af30-4521-9b56-3bdf0a8d1a15.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=8864&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=8864&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=8864&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 17 - Jul 19](https://www.expedia.com/Hotel-Search?regionId=8864&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Middletown cottages ![Exterior](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w919h683x47y0-1b7c08f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w506h683x259y0-6b740411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w506h683x259y0-81ebd497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w905h683x60y0-1d21c342.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hello Small Stone [](https://www.expedia.com/Middletown-Hotels-Hello-Small-Stone.h99261544.Hotel-Information) Middletown 9.6/10 Exceptional (5 reviews) "The house was great. It was nice to sit and relax by the small pond in the back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John H. $389 nightly $440 total Apr 8 - Apr 9 Total with taxes and fees [](https://www.expedia.com/Middletown-Hotels-Hello-Small-Stone.h99261544.Hotel-Information) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369793/d5ed89f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Living area](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369793/780cac79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369793/1d322732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369793/18ffe7af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hike & Fish: Outdoor Retreat Near Trails [](https://www.expedia.com/Hike-Fish-Outdoor-Retreat-On-The-Basher-Kill.h114369793.Hotel-Information) Westbrookville $272 nightly $308 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Hike-Fish-Outdoor-Retreat-On-The-Basher-Kill.h114369793.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/83000000/82540000/82537300/82537288/1e61a43b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/83000000/82540000/82537300/82537288/5178d297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/83000000/82540000/82537300/82537288/68236176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82540000/82537300/82537288/e668d22e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around [](https://www.expedia.com/Sparrow-Bush-Hotels-Serene-Lakeside-Oasis-Fast-WiFi-15-Hrs-From-NYC.h82537288.Hotel-Information) Sparrow Bush 9.4/10 Exceptional (11 reviews) "A little off the beaten path, but a lovely Vrbo with excellent amenities with a nice natural surrounding." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas G. $257 nightly $291 total Apr 13 - Apr 14 Total with taxes and fees [](https://www.expedia.com/Sparrow-Bush-Hotels-Serene-Lakeside-Oasis-Fast-WiFi-15-Hrs-From-NYC.h82537288.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/dd263f18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/3008d822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/54004000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/b2f29274.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relaxing Farm Cottage Escape, 10 Min from LEGOLAND [](https://www.expedia.com/Goshen-Hotels-Relaxing-Farm-Cottage-Escape.h78138015.Hotel-Information) Goshen 9.8/10 Exceptional (13 reviews) "Great place to stay when visiting Legoland. Convenient location and comfortable and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica C. $281 nightly $293 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Goshen-Hotels-Relaxing-Farm-Cottage-Escape.h78138015.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/3a9ea66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/5ed95c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/e56d490f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/c55e3667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands [](https://www.expedia.com/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) Fort Montgomery 9.8/10 Exceptional (134 reviews) "Amazing place Thanks for the stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julien C. $270 nightly $305 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/dabdeda4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, books](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/4fbee988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/c4f41298.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, books](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/cd189b6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks [](https://www.expedia.com/Kerhonkson-Hotels-Dream-Cottage-In-The-Gunks.h83439008.Hotel-Information) Kerhonkson 9.4/10 Exceptional (13 reviews) "Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick S. $179 nightly $181 total Apr 9 - Apr 10 Total with taxes and fees [](https://www.expedia.com/Kerhonkson-Hotels-Dream-Cottage-In-The-Gunks.h83439008.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113160000/113159700/113159615/5de49e46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113160000/113159700/113159615/ffdabe30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113160000/113159700/113159615/d4499593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113160000/113159700/113159615/6a029a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro [](https://www.expedia.com/Bloomingburg-Hotels-Charming-Cottage-In-The-Lower-Catskills-Near-Ellenville-And-Wurtsboro.h113159615.Hotel-Information) Bloomingburg 10/10 Exceptional (1 review) "The place was as described, quaint, clean, no issues with communication or check in" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen H. $190 nightly $214 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Bloomingburg-Hotels-Charming-Cottage-In-The-Lower-Catskills-Near-Ellenville-And-Wurtsboro.h113159615.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108780000/108777400/108777320/w3379h2254x65y113-3bf6be6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108780000/108777400/108777320/w2205h3380x137y65-0561b2fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/109000000/108780000/108777400/108777320/w3378h2246x65y117-b9d7217d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108780000/108777400/108777320/70357fc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike [](https://www.expedia.com/Vernon-Hotels-Luxe-10-Guest-Cottage-SkiGolfFire-PitLakesHike.h108777320.Hotel-Information) Vernon Township 8.8/10 Excellent (3 reviews) "House was beautiful! Airy, cool and bedrooms were comfortable! Such a cute cottage and outdoor fire pit was amazing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cherlyn I. $422 nightly $477 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Vernon-Hotels-Luxe-10-Guest-Cottage-SkiGolfFire-PitLakesHike.h108777320.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-04-11&endDate=2026-04-12®ionId=8864&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=CABIN) Cottages [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=COTTAGE) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=VACATION_HOME) Villas [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=VILLA) Condos [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=CONDO) Apartments [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=APARTMENT) Chalets [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=CHALET) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=APART_HOTEL) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FMiddletown-Cottages.d8864-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMiddletown-Cottages.d8864-aaCottages.Travel-Guide-Accommodation) ## Top Middletown Hotel Reviews ![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/8648b91b_y.jpg) ### Holiday Inn Express Hotel & Suites Chester by IHG 8/10 Good "Everything was good, place just needs alot of updates " [](https://expedia.com/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Middletown-Goshen](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/26de74c3_y.jpg) ### La Quinta Inn & Suites by Wyndham Middletown-Goshen 10/10 Excellent "Breakfast good parking safe" [](https://expedia.com/Middletown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Middletown.h4098.Hotel-Information) ![Resorts World Catskills Casino](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/0479130a_y.jpg) ### Resorts World Catskills Casino 8/10 Good "Close parking, good food choices, nice spa and pool." [](https://expedia.com/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information) ![The Kartrite Resort & Indoor Waterpark](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/7b139e0a_y.jpg) ### The Kartrite Resort & Indoor Waterpark 10/10 Excellent "Had a great time " [](https://expedia.com/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.Hotel-Information) ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/38c7288e_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 8/10 Good "Convenient, clean and friendly.. " [](https://expedia.com/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Overlook Lodge at Bear Mountain](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/679bdd4c_y.jpg) ### Overlook Lodge at Bear Mountain 10/10 Excellent "Very good experience " [](https://expedia.com/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Courtyard by Marriott Middletown Goshen](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/5a64b5a6_y.jpg) ### Courtyard by Marriott Middletown Goshen 10/10 Excellent "Very clean " [](https://expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ![Hampton Inn by Hilton Middletown](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/88d2ecc5_y.jpg) ### Hampton Inn by Hilton Middletown 2/10 Terrible "so smelly" [](https://expedia.com/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information) ![Super 8 by Wyndham Middletown](https://images.trvl-media.com/lodging/1000000/460000/459800/459783/d86611d0_y.jpg) ### Super 8 by Wyndham Middletown 2/10 Terrible "V" [](https://expedia.com/Newburgh-Hotels-Super-8-By-Wyndham-Middletown.h459783.Hotel-Information) ## Find out more about Middletown ## Middletown Cottages information | Number of reviews | 166 | | ----------------- | ------------ | | Accommodation | 134 Cottages | | Lowest Price | $181 | | Highest Price | $440 | ## Frequently asked questions ### Why book your cottage in Middletown with Expedia? ### How can I find cheap cottages in Middletown? ### What is there to do in Middletown near my cottage? ## Explore a world of travel with Expedia - 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